How about right after you score the winning touchdown in a college bowl game, ensuring your team remains undefeated?
I still like how I proposed to Jaime, a more old-fashioned way, but man I bet that was enjoyable for the star player from Boise State!
As far as how I proposed to Jaime…Two years ago (my goodness time travels fast), I invited Jaime up to Boston (she was living in New York City). I told her to dress nicely because we were going to go to a nice restaurant. I did not tell her which restaurant, or it might have given it away. I already had a ring, and had already called her father for approval. (He thankfully remained silent, but did give her a hint–she didn’t catch it thankfully). We began our date by going to the Museum of Science in Boston, about as benign as you can get on a date. It’s a great museum, and they had a nice show about Cassini and the satellite’s arrival at Saturn.
We had some extra time before our scheduled dinner at the restaurant, and we went to the Prudential place, where we walked around in the mall. Jaime saw a jewelry store and asked if we could go look at rings. Doh! What to say! I had the ring in my pocket. I didn’t want her to look at any rings and find one she liked that wasn’t going to be the one I was going to give her, so I told her, “I put money down already on a ring.” That was truthful, without requiring to tell her I already bought the ring, and had it waiting in my coat pocket!
So it came time to go to the restaurant. I told Jaime which restaurant we were going to. It is called Top of the Hub and is located on the 52nd floor of the Prudential Tower, overlooking all of Boston, a gorgeous view. We went up to the restaurant. I had previously called a flower shop to have flowers delivered to the restaurant. Once seated, we ordered our appetizers. At this point, Jaime could see that something was deeply on my mind, and she asked “what are you thinking?” I did not answer her, but I told her that I needed to excuse myself briefly. I told her I would be right back.
I walked away to the maitre d’ and picked up the flowers. I took a deep breath and walked back to Jaime, handing her the flowers and kneeling down on one knee. I began reciting a poem I wrote for this occasion (which later became a song I wrote to her), and as I finished, pulled out the engagement ring, asking Jaime to marry me. She said yes. The restaurant exploded in cheers and applause.